Dimethyl Sulfoxide → HCID 57988793, compound

HRID 889012Notes

Reaction equation

[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][N:25]([CH2:27][C:28]#[CH:29])[CH:26]=3)=[N:8][C:7]=2[N:6]([CH2:30][CH2:31][CH3:32])[C:5]1=[O:33])[CH2:2][CH3:3].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C=O.[CH3:43]S(C)=O>O.[Cu]I>[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:43][C:29]#[C:28][CH2:27][N:25]2[CH:26]=[C:22]([C:9]3[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:21])[CH3:19])[C:11]4[C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:33])[N:6]([CH2:30][CH2:31][CH3:32])[C:7]=4[N:8]=3)[CH:23]=[N:24]2)[CH2:37][CH2:36]1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of 1,3-dipropyl-8-(1-prop-2-ynyl-1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.1 g, 0.212 mmol), N-methyl piperazine (0.025 g, 0.254 mmol), formaldehyde (0.08 ml), CuI (0.008 g), and DMSO (2 ml) was stirred at 30° C. for 72 hours. The mixture was cooled to 25° C. and the residue was diluted with water (10 ml) and extracted with ethylacetate (2×10 ml). The organic layer was washed with saturated brine solution (50 ml) and dried over Na2SO4. The solvent was evaporated to obtain pure 8-{1-[4-(4-Methyl-piperazin-1-yl)-but-2-ynyl]-1H-pyrazol-4-yl}-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.105 g, 85%).

Workup

temperatureThe mixture was cooled to 25° C.
extractionextracted with ethylacetate (2×10 ml)
washThe organic layer was washed with saturated brine solution (50 ml)
dry with materialdried over Na2SO4
customThe solvent was evaporated

Sources & evidence

ORD record: ord-e9a6bd4ca36549a890fb6fba445d4f4c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252797B2

Reaction notes

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